Hydrochloric Acid → HCID 22319295, compound

HRID 497513Notes

Reaction equation

HRID 497513 reaction equation
C[O:2][C:3](=[O:18])[CH:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:8]=1)[CH2:5][CH3:6].[OH-].[Na+].Cl>CCO.O>[CH2:14]([O:13][C:10]1[CH:9]=[CH:8][C:7]([CH:4]([CH2:5][CH3:6])[C:3]([OH:18])=[O:2])=[CH:12][CH:11]=1)[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20872826HCID 20872826, compound

Product 1

HCID 22319295HCID 22319295, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(Scheme 2, Compound F) To a solution of 2-(4-butoxy-phenyl)-butyric acid methyl ester (2.0 g, 8.0 mmol) in EtOH (30 mL) was added NaOH (10 N, 6 mL, 60 mmol). The resulting mixture was stirred at rt for 3 hours, diluted with H2O (30 mL), acidified to pH˜1.0 using HCl (6N). The precipitates were filtered off by filter paper, washed by H2O and hexanes. This compound was obtained as a white solid. (1.4 g, 5.9 mmol, 74% yield). 1H NMR (DMSO-d6) δ 12.20 (br. s, 1H), 7.16 (d, 2H, J=7.0 Hz), 6.87 (d, 2H, J=8.5 Hz), 3.92 (t, 2H, J=6.5 Hz), 3.31 (t, 2H, J=6.9 Hz), 1.93 (m, 1H), 1.63 (m, 3H), 1.42 (m, 2H), 0.97 (t, 3H, J=7.2 Hz), 0.79 (t, 3H, J=4.0 Hz).

Workup

  1. filtrationThe precipitates were filtered off
  2. filtrationby filter paper
  3. washwashed by H2O and hexanes
  4. customThis compound was obtained as a white solid

Sources & evidence

ORD record
ord-341003cc985d4a2bbc4ba979f835af30
Source dataset
uspto-grants-2005_09
Patent number
US06949574B2

Reaction notes

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